Ethanol hydrochloride → HCID 136174528, compound

Participants

Reaction Steps

tert-Butyl (10S)-6-amino-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate (130 mg, 0.383 mmol) was treated with 10 mL of 3.0 M HCl/EtOH and heated up to reflux for about 20 minutes. The volatiles were then removed under reduced pressure, and the resulting residue was partitioned between CH2Cl2 and H2O. The layers were separated, and the aqueous one was extracted again with CH2Cl2, and the combined organic layers were discarded. The aqueous layer was then treated with concentrated ammonium hydroxide solution until the pH ˜11. The layer was extracted with CH2Cl2 (3×). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give a white solid. Chromatography (SiO2, 20-40% CMA/CHCl3) afforded (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (55 mg) as an off white solid, m.p. 265-273° C.

Provenance & Evidence